Acetyl chloride → HCID 54043249, compound

Participants

Reaction Conditions

Reaction Steps

Acetyl chloride (50 mL, 0.70 mmol) is added slowly to a solution of 2-[(1-tert-butoxycarbonylamino-cyclopentanecarbonyl)-amino]-3-[4-(piperidin-3-yl)-phenyl]-propionic acid ethyl ester (277 mg, 0.57 mmol) and 11 mL (0.79 mmol) of Et3N in 2 mL of CH2Cl2. The reaction mixture is stirred at 0° C. for 2 h, and then partitioned between saturated aqueous NaHCO3 solution and CH2Cl2. The organic phase is washed with brine, dried over MgSO4, filtered, and concentrated. The residue is purified by chromatography on silica gel (EtOAc) to furnish 2-[(1-tert-butoxycarbonylamino-cyclopentanecarbonyl)-amino]-3-[4-(1-acetyl-piperidin-3-yl)-phenyl]-propionic acid ethyl ester; 1H NMR (300 MHz, CDCl3) δ7.00-7.15 (m, 4 H), 4.80-4.90 (m, 1 H), 4.70 (br t, 2 H), 4.15 (q, 2 H), 3.00-3.15 (m, 3 H), 2.45-2.70 (m, 2 H), 2.12, 2.08 (s each, 3 H) 1.95-2.40 (m, 6 H), 1.50-1.95 (m, 8 H), 1.40 (s, 9 H), 1.20 (t, 3 H).

Provenance & Evidence